Home Vacation Rentals By Owner In Wellfleet, MA

Showing 200 Of 344 Vacation Rentals
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Exceptional(1)

$457.3

/ Nightly
Private Vacation Home

Sandy beach cottage on Wellfleet Bay

Wellfleet, Massachusetts, United States

`Light on the Mayo` is a newly built, finely appointed, 2-bedroom, 1-bathroom cottage located across the road from the famous `Mayo (swim) Beach` in Wellfleet Bay. brbrThe cottage was built in 2018 and is incredibly cozy with unobstructed views of Mayo Beach and Wellfleet Harbor. It also has excellent privacy and high-end amenities. The house includes central heat and air conditioning in each bedroom as well as the living room. It has a modern kitchen with a beautiful dining nook.brbrLight on the Mayo is located on famous Kendrick Avenue which is one of the best swim beaches on the Cape w/ ultra warm water and soft sand. A short walk down the road is a large playground with play-structure, tennis, pickleball pickleball and basketball courts as well as an outdoor theater and - of course - the town pier. Fishing, boating, and creemies with `jimmies`. brbrDowntown Wellfleet is 2 miles away with cute stores, fish markets, and great restaurants.brbrTidal Info! Wellfleet bay is world famous for it`s oysters in large part because the low tide goes out more than 1/2 a mile! It makes for fun exploring but it also means no swimming at low tide. Schedule appropriately!brbrBeach Stickers! At low tide, or for a change of pace use your VRBO receipt to get a weekly beach sticker to visit the ponds and oceanside for swimming. Big waves, huge dunes on the ocean or crystal clear freshwater ponds.brbrParking for two cars adjacent to the cottage. Two restaurants and the pier (fried takeout) are within walking distance of the Light. Plenty to do during the day without the need to drive.
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Bath 1

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Sleep 4

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Exceptional(4)

$1602.3

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Private Vacation Home

Historic farmhouse in charming Wellfleet

Wellfleet, Massachusetts, United States

This 1820 Cape Cod with two attached barns is a historic treasure in the heart of Wellfleet. Filled with antiques, layers upon layers of colors, and whimsical and historic treasures throughout, this home offers so much to occupy the eye and imagination. Listed on the national historic registry, this home has been meticulously restored — preserving all of its charm and character but with state of the art, modern amenities. This farmhouse has 5 bedrooms each with its own en-suite full bathroom. The well-appointed kitchen occupies what was formerly the milking barn and is adorned with the most beautiful light throughout the day. The kitchen boasts a 48” AGA induction range, subzero refrigerator, wine fridge, two dishwashers, and an 11 foot island. It is a chef’s dream kitchen. Enjoy meals with family and friends in the dining room imagining all of the stories told through its 200 year history. The crown jewel of the home is the restored post and beam barn and loft— it is the perfect place to spend time with loved ones or simply take a nap. And down below, enjoy the speakeasy-like bar and pool table room for late night fun.br In the quaint town of Wellfleet, this home will be a featured in the 2025 Wellfleet Historical House tour. Located less than a block away from Main Street, you will be in walking distance of the town’s famous art galleries, restaurants, artisan and pottery shops. It feels amazingly secluded despite being so close to town. In 1820, Richard and Priscilla Newcomb cleverly built the home where it still stands today. When you approach the house, you will immediately notice its unusual orientation to the street. The light cast throughout the home is simply beautiful. Dozens and dozens of original, restored windows carry breezes throughout. Hand hewn beams, antique wide pine planks, the post and beam construction has all been lovingly preserved to give us a glimpse into a different time in American history. The bay is less than a 1 mile walk and the Ocean side beaches are just a little over 2.5 miles and with access to Wellfleet’s freshwater kettle ponds, everything is right there for you to enjoy. brbrThere is a massive private courtyard adjoining the 4 structure compound to spend evenings dining al fresco, entertaining or just spending time relaxing outdoors.brbrThis home is authentic in every way.
Bed 5

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Bath 5

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Sleep 12

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Exceptional(1)

$427.29

/ Nightly
Private Vacation Home

Spacious & Well-Equipped 3BD--A/C, Sun Room, Close to Wellfleet's Wonderful Ponds

Wellfleet, Massachusetts, United States

Walk to Duck Pond!brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrThis spacious three-bedroom contemporary home is an ideal summer vacation retreat! Situated on a wooded lot in a quiet neighborhood, the home is close to Wellfleet's beloved freshwater ponds. The first floor has an open kitchen, dining and living area. Large windows let in plenty of light. The living room has comfortable seating and the kitchen is well-equipped. brbrThere is a wonderful sun room with comfortable seating, a television and a table perfect for games and puzzles. There is also a large master bedroom with ensuite bath (shower only) on this floor as well as a half bath. brbrThe second floor has an open loft that overlooks the living area--a quiet place to enjoy a book or watch a movie. Beyond the loft is a bedroom with a queen bed. The other bedroom on this floor has two twin beds. There is also a shared full bathroom with tub and shower on this floor. brbrThe home has central air conditioning, cable, WiFi and first floor washer/dryer. The outdoor space is lovely--a patio with table and chairs, gas grill and an enclosed outdoor shower. brbrOn Wellfleet's desirable ocean side, you are a mile walk through Cape Cod National Seashore woods to Duck Pond and a mile drive to Great Pond. Continue on down Cahoon Hollow Road to the amazing ocean beaches and the Beachcomber! Head into Wellfleet Center and Harbor for restaurants, galleries, shopping and live entertainment. Short drive to Cape Cod National Seashore sites and beaches, the Cape Cod Rail Trail, Wellfleet Bay Wildlife Sanctuary, tennis and golf. brbrAdditional Fee: $220 non-refundable reservation fee; $30 damage protection fee (no security deposit required); guest services fee; all applicable taxesbr* FREE WIFI br* SATURDAY TO SATURDAY RENTALbr* NO PETSbr* NO SMOKINGbr* OCCUPANCY: 6 (Adults and children)br* PARKING FOR 3 VEHICLESbr* Sheets and towels providedbrbr**** FREE ACTIVITIES INCLUDED ****brTo enhance your vacation experience, Kinlin Grover Compass includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area. brbrAs a guest of Kinlin Grover Compass, you'll receive free tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities! Activities and availability are subject to change. Not available on stays over 28 days.brbr**** CANCELLATION/REFUND POLICY ****brUpon cancellation for ANY reason, money will be refunded less a 20% service fee of the total rental amount due, ONLY if the property is re-rented for the same terms and conditions of the original Agreement. Tenant further acknowledges and agrees that where Kinlin Grover Compass undertakes to re-let the property, the rental fee to be charged to the substitute tenant shall be in an amount to be determined in the reasonable discretion of Kinlin Grover Compass and Owner. Tenant agrees that any cancellation of the reservation, undertaken at any time, shall not be effective unless in writing and delivered to Kinlin Grover Compass.brbrKGC WSTEFA
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Bath 2

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Sleep 6

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Exceptional(30)

$827.63

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Private Vacation Home

Watch the Sunset from this Bayfront Home! (1349)

Wellfleet, Massachusetts, United States

***NEW FOR 2026, AC*** Experience the magic of Cape Cod Bay from this spacious, contemporary home on Bound Brook Island, where peace, privacy, and breathtaking sunsets await. With direct beach access and sweeping water views, this five-bedroom, three-bath retreat comfortably hosts up to 10 guests—perfect for large families or groups looking for a true coastal escape.brbrDesigned for relaxation and convenience, the home offers two bedrooms on the main level—one with a queen bed and one with two twins—ideal for guests who prefer first-floor living. The second level features three additional bedrooms: one with a king bed, one with a queen, and one with two twin beds, providing plenty of room for everyone to settle in.brWith 2,440 sq. ft. of living space, there is room for everyone to spread out and enjoy time together. The property includes a screened porch, inviting living areas, satellite TV, washer/dryer, and a full kitchen well-equipped for preparing fresh seafood and favorite meals. Step outside to the expansive deck to take in unforgettable sunsets over the bay, or head down the private stairs to enjoy the sandy beach below. After a day on the shore, rinse off in the outdoor shower.brbrWell-behaved dogs are welcome with an additional pet fee, making this a wonderful choice for families traveling with a furry companion.brbrPLEASE NOTE: Only 4 cars allowed. One to be parked in the garage the other three parked in front of it. Do not block access to house on right. **NOTE: Road to house is a long, dirt road for a couple miles. One lane traffic. Please be aware that road access to the home may be temporarily limited due to storm surge or weather conditions. We recommend checking local updates and planning accordingly. 3 night minimums available in off season. An administrative fee and applicable taxes may apply. Linens are not provided—guests may bring their own or rent.
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Sleep 10

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Exceptional(4)

$397.72

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Cottage

2 Bedroom Cottage With Private Beach Access (1688)

Wellfleet, Massachusetts, United States

Enjoy the best of Cape Cod from this inviting two-bedroom cottage, ideally located within the Wellfleeter Condominium complex at the end of Mayo Beach on beautiful Wellfleet Bay. With a private path leading to 400 feet of shared sandy beachfront, this cozy retreat offers a relaxed coastal setting perfect for a memorable seaside escape.brbrInside, the cottage features a comfortable living room, a kitchen and dining area for easy meals at home, and two bedrooms—one with a double bed and the other with two twin beds—comfortably accommodating up to four guests. The bathroom includes a walk-in shower. Air conditioning and WiFi add everyday comfort and convenience.brbrVenture outside and stroll along the path to the private sandy beach, ideal for morning walks, beachcombing, or enjoying peaceful bay views. The cottage is close to public tennis courts, a community playground, local restaurants, and the lively Wellfleet Harbor area. Downtown Wellfleet is just over a mile away, offering charming shops, galleries, and dining. Freshwater ponds and ocean beaches are also a short drive from the property. With its charming simplicity, private beach access, and unbeatable location, this cottage is a wonderful choice for your Wellfleet getaway.brbrCottage is available for an off season 3 night minimum with an added cleaning fee. Save the cleaning fee by booking 7 or more consecutive nights. An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.
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Bath 1

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Sleep 4

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Exceptional(12)

$430.44

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Private Vacation Home

Historic Home on National Seashore Land (1374)

Wellfleet, Massachusetts, United States

This comfortable antique home is located on several acres of land within the National Seashore, just 1/4 mile to Bound Brook Island Beach. Within OYSTER, the main house, you will find three bedrooms and two full baths. (One recently renovated main floor full bath with a tub/shower combo, one slightly smaller 2nd floor full bathroom with tub/shower combo) The interior is unique with comfortable furnishings. The main level has an L-shaped living room, dining room, fully equipped kitchen, an adjacent den, full bath, and one bedroom with a queen sized bed. On the second level are two more bedrooms, one with a queen bed and the third with two twins that easily convert to a king bed, if you like. The fourth bedroom included in this rental which offers a queen bed is accessible by walking out of the main part of the home to a small cottage behind the house. This space has its own full bath with a walk in shower. If you need even a little more space, there is an additional rental home just down the driveway (approximately 500 feet) offering 2 bedroom, shower bath, large bay window, TV, door to private lawn area, table & chairs, small fridge, sink and coffee pot available to rent as well. (see sister listing 695 Bound Brook Island Rd. CATTAIL) There is a brick patio that spans the front of the home and a large yard with mature landscaping for your pleasure. **NEWLY CONSTRUCTED RAISED ROAD FOR 2026*** Enjoy unrestricted ease of access to this sanctuary property nestled in the privacy of the National Seashore. Mosquito Squad regularly treats this property and homeowner welcomes input and feedback if additional treatments are needed. 3 night minimums available with an added $300 cleaning fee. Save the cleaning fee by booking 7 or more consecutive nights. An administrative fee and applicable taxes may apply. Linens are not provided—guests may bring their own or rent. This property does not have air conditioning.
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Bath 3

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Sleep 8

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Exceptional(2)

$745.83

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Private Vacation Home

Beautiful Sunsets Over Lieutenant Island (1371)

Wellfleet, Massachusetts, United States

Set against the backdrop of Lieutenant Island and surrounded by Audubon conservation land, this spacious 4-bedroom, 3-bath home offers a peaceful Cape Cod escape with unforgettable sunset views over Cape Cod Bay.brbrThe first floor welcomes you with an open layout that includes a fully equipped kitchen, dining area, comfortable living room, sunroom, and screened porch—perfect for breezy summer evenings. A first-floor bedroom with two twin beds provides added convenience. Upstairs, you’ll find three additional bedrooms, including a primary with a king bed and two more rooms, each with twin beds, accommodating up to 8 guests with ease.brbrOutdoors, the wraparound deck and widow’s walk are ideal for soaking in the views, while the private yard and screened porch offer great spaces for family gatherings. Fire up your choice of a charcoal or gas grill, rinse off in the outdoor shower after a beach day, and relax as the sun dips below the horizon.brbrLocated in a serene natural setting, yet close to Wellfleet’s beaches, trails, and town center, this home combines comfort, space, and an unbeatable location.br*PLEASE NOTE: Insinkerator and fireplace NOT to be used. An administrative fee and applicable taxes may apply. Linens are not provided—guests may bring their own or rent. This property does not have air conditioning.
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Bath 3

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Sleep 8

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Exceptional(9)

$538.38

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Private Vacation Home

Newly Built Contemporary with Central Air, Ocean Side of Wellfleet (2045)

Wellfleet, Massachusetts, United States

Welcome to this beautifully crafted, newly built contemporary home designed with comfort, style, and relaxation in mind. Ideally located on the ocean side of Wellfleet, this light-filled retreat is just a short drive to scenic Oceanview Drive, stunning ocean beaches, and Wellfleet’s beloved freshwater ponds—perfect for a classic Cape Cod getaway.brbrThe home comfortably sleeps up to eight guests across four thoughtfully appointed bedrooms, each featuring a queen bed. The first floor offers three bedrooms, a full bathroom, and a cozy media area with a flat-screen TV—ideal for movie nights or winding down after a day at the beach.brbrUpstairs, the open-concept living space is the heart of the home, showcasing cathedral ceilings, abundant natural light, and large windows overlooking the backyard. The fully equipped kitchen features stainless steel appliances, a gas range, and ample space to prepare family meals. An oversized dining table easily accommodates everyone for meals, games, or evening gatherings, while a convenient half bath adds to the home’s thoughtful layout.brThe private primary suite is also located on the second floor and includes a queen bed, an ensuite bathroom, and a walk-in closet—your own peaceful retreat after a day of exploring.brbrStep outside to enjoy the spacious backyard, deck with gas grill and outdoor seating, and the enclosed outdoor shower—perfect for rinsing off after a beach day. A screened-in porch adds an extra space to relax with your morning coffee or unwind in the evening. Recent updates as of 2024 include a new couch in the media area, new air conditioning, a new kitchen stove, an improved parking area, and newly planted trees. With central air conditioning, modern amenities, and a prime Wellfleet location, this custom-designed home is a wonderful choice for families or groups looking to enjoy the best of Cape Cod.brbrThree-night minimum stays are available in the off-season (with an added cleaning fee), and the cleaning fee is waived for stays of seven nights or more. An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.
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Bath 2

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Sleep 8

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Exceptional(13)

$666.52

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Private Vacation Home

Find Your Wellfleet Vacation in this Stunning Home (1682)

Wellfleet, Massachusetts, United States

Discover the perfect Cape Cod escape in this newer construction, spacious 3-bedroom, 2.5-bathroom contemporary Cape-style home. Centrally air-conditioned and set in a private location, this property is just two miles from Indian Neck Beach and ready to host up to 7 guests.brbrThis home is designed for comfort and outdoor enjoyment. Sip your morning coffee and read the newspaper on the peaceful screened porch at the rear of the house. After a fun-filled day at one of the many local beaches, rinse off in the large outdoor shower and then unwind on the charming wrap-around farmer's porch that spans two sides of the house. The lovely yard offers ample space to lounge and relax, and you can grill out on the gas grill on the patio.brbrThe main floor is bright and open, consisting of the living, dining, and full kitchen areas (complete with a dishwasher and lobster pot), a half bath, and a primary bedroom suite. The primary bedroom features a comfortable king bed and an ensuite bath with a shower. Of note, the door casement to the primary bedroom and the ensuite bathroom are handicapped accessible. The second floor hosts two more bedrooms: one with two twin beds and the other with one queen and one twin bed. This floor is completed by a cozy loft/sitting area and a full bathroom with a tub and shower. Enjoy modern amenities throughout, including Central Air Conditioning, Wi-Fi, and a washer and dryer.brbrThe Indian Neck Beaches are approximately 2 miles away, making for a pleasant bike ride or short drive. It is about 5 minutes by car to Wellfleet Center and just a little farther to the famous pond and ocean beaches. Best of all, you can bring along your hypo-allergenic, non-shedding dog (20 lbs or less) for an added fee! Driveway parking is available for up to four cars.br Available for 3 night minimums with an added cleaning fee. 7 night reservations include the cleaning fee. An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.
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Sleep 7

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Exceptional(14)

$229.72

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Cottage

Sweet Cottage Retreat Near Cape Cod Beaches! (2080)

Wellfleet, Massachusetts, United States

Discover your charming home base for a Cape Cod adventure! This cozy 1-bedroom, 1-bath cottage is part of the quaint Salt Box Condominium complex, offering a perfect, peaceful retreat for two guests. With its fantastic central location, you'll enjoy quick access to both stunning ocean and bay beaches, as well as picturesque freshwater ponds. This cottage is all about maximizing your relaxation and convenience.brbrStep inside to find an inviting open floor plan encompassing the kitchen, living room, and dining area, all designed for comfort and easy living. The good-sized bedroom provides a peaceful sanctuary, featuring a plush King bed and an attached full bathroom with a shower stall. The entire space flows seamlessly to one of the cottage's best features: the screened-in porch.brbrThe screened-in porch, accessible directly from both the main living area and the bedroom, offers plenty of seating and overlooks tranquil woods, making it the ideal spot to enjoy your morning coffee, relax after a day at the beach, or dine al fresco. A gas grill is also provided for your use, making outdoor meals a breeze.brbrWhile you enjoy the quiet seclusion of the condo complex, you are just a short drive away from everything the Cape has to offer, including the town center, great restaurants, local golf courses, and the classic Drive-In Movie theatre. The cottage is equipped with an A/C window unit, ceiling fans, and robust WiFi. For entertainment, a Smart TV is provided; however, please note it is not connected to cable, so guests should plan to bring a Roku or other smart device for streaming services.brbr3 night minimums available for an added cleaning fee. Save the cleaning fee by booking 7 or more consecutive days. An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.
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Sleep 2

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Exceptional(8)

$387.08

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Private Vacation Home

Indian Neck Cottage with Beautiful Views (1310)

Wellfleet, Massachusetts, United States

If you’re seeking a true Cape Cod getaway with stunning harbor views and the charm of simple coastal living, this Indian Neck cottage is the perfect choice. Set on a single level and designed for easy vacation living, this home offers everything you need for a memorable stay in Wellfleet.brbrThe cottage accommodates up to 6 guests across three comfortable bedrooms—one with a queen, one with a double, and one with three twin beds. A full bath, cozy living room, and eat-in kitchen provide all the essentials for a relaxing vacation, while the back deck spans the length of the home, offering peaceful space to unwind and take in the serene views of Wellfleet Harbor.brFurnishings are rustic, clean, and durable, with a focus on comfort and relaxation. Enjoy convenient amenities including Wi-Fi, gas grill, and both indoor and outdoor gathering spaces. After a day at the beach, rinse off in the outdoor shower and enjoy a Cape Cod evening under the stars.brbrThis “pet-friendly” rental welcomes well-behaved dogs with an additional pet fee, making it a great option for families and dog lovers alike. Short stays are available with an added cleaning fee, which is waived for stays of seven nights or longer.brPlease note: linens are not provided but may be brought from home or rented. This property does not have air conditioning. Administrative fees and applicable taxes may apply.brbrFor guests looking for value, views, and a classic Cape Cod experience, this Indian Neck cottage delivers the perfect seaside retreat.
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Bath 1

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Sleep 6

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